Entrepreneurship – What It Takes

Entrepreneurship runs deep within my family. In the past five generations, four of those have listened to the call of being one’s own boss. This went back to my great-great grandfather in Palestine who accumulated a lot of land and in the earliest part of the 20th Century started planting orange trees until he owned one of the largest orchards in the country.

He sired ten sons, probably to help him move from a peasant farmer to a gentleman farmer. It seems sons were cheaper than livestock. The entrepreneurial bug skipped many of his ten sons, which included my great grandfather…which is why the family tree is four for five entrepreneurial generations. My great granddaddy did not hear, feel, nor even smell the calling.

In 1948, after the creation of the state of Israel, all the land and oranges were lost to the new state, although one of my cousins still has the land deeds somewhere. But that story is for another essay. What follows is my first attempt at trying to explain what I believe it takes to be an entrepreneur.

The Calling

The “calling” for an entrepreneur is powerful as that for the priesthood or nunnery. It is existential even more than economic impulse. To be sure many become entrepreneurs through circumstances like being fired, but the vast majority of us travel our own path because we cannot NOT answer the “call”. I am not trying to be metaphysical here, but explaining the source of passion that drives entrepreneurs. If you are lacking in this drive, you may want to opt out.

So after one answers the call to become an entrepreneur, what else is necessary to make a go of it? After tasting success and failure several times, I think there are a few heuristics that have emerged in my mind. These rules of thumb are not set in concrete, but they are pretty good rules that apply in most cases.

Operational Speed

“A Good plan violently executed now is better than a Perfect plan executed next week.”–General George S. Patton

I am fond of saying that one does not have to be the best chess player to win a match if you can move twice for every time your competitor moves once. You can even have significantly less resources at your disposal and still come out on top. Try this. Sit down with a better chess player than yourself and let your opponent pick any three pieces (except the King) to take from your side of the board before the game begins.

This puts you at a disadvantage regarding resources for the game. Now, start playing with a new rule where you move twice for every time your opponent with more resources moves. Play the game until someone is in checkmate. Even with less initial resources, you will most likely win more times than not. Try it.

The metaphor holds for entrepreneurs. Those that join entrepreneurial ranks from large corporations often cannot get the rhythm of moving twice as fast as their competitors. Large companies with all the controls, politics, fear, and CYA (cover your ass) mentality fosters an operational mindset that kills speed. But experienced entrepreneurs understand Patton’s quote.

Successful entrepreneurs are bold if nothing else.

Fear of Failure

“If you want to conquer fear, don’t sit home and think about it. Go out and get busy.“–Dale Carnegie

If you think entrepreneurs who are risking everything do not have fear, you are simply mistaken, but they are not paralyzed by that fear. Courage is not the absence of fear. It is about conquering that fear and not letting it have power over you. For real entrepreneurs, failure does not bring shame. Walt Disney, Henry Ford, Colonel Sanders and Fred Smith are just a few that failed miserably (or honorably if you like). My father failed spectacularly a couple of times before retiring when he was 49. I went bust more than once before experiencing success.

There is no question that I learned more from failures than my successes. Don’t get me wrong, failing was not fun, but the lessons learned are hard wired and prepared me. If you are the type that is defined by failure (or success), maybe entrepreneurship is not right for you.

Tinkering

“Tinkering by trial and error has traditionally played a larger role than directed science in Western invention and innovation…we must recognize that there is an inverse relationship between the amount of formal education that a culture supports and its volume of trial-and-error by tinkering.” –Nassim Taleb

I think we have more MBAs in the US than factory workers. MBAs are generally theory driven and entrepreneurs must resist “experts” that interfere with the business of doing. Theory is fine, but doing is even better. Tinkering becomes a way to improve quicker. Think of evolution. Nature tinkers in a non-directed manner and introduces many more failed tests than successes.

Start-ups need to test, try and move over and over. Related to operational speed, entrepreneurs must evolve or die. As is often the case, resources may be more limited than competitors, but you can still find hundreds of things that lend themselves to tinkering your way to solutions. Just make sure you manage the downside. Tinkering suggests smaller “tweaks” than major shifts.

Trial and error has a bad rap in the 21st Century world where we like to think of imposing some algorithmic top down solution. Tinkering is bottom up and much more humble. It is hypothesis driven rather than driven by someone else’s theory. With enough tinkering, you can start with an amoeba and eventually evolve to an elephant.

Embracing Uncertainty

“For my part I know nothing with any certainty, but the sight of the stars makes me dream.”–Vincent van Gogh

I saved the most difficult for last. I wrote about this in more detail here:

We all crave to know what is going to happen. In business we have a term, “visibility”. Who does not want to see through the fog? This desire has created an industry hooked on predictive methodologies. This has been in tandem with our ability to collect more and more data. I will not go into a treatise today on how more data does not bring better prediction.

So what do I mean that entrepreneurs need to embrace uncertainty? Stop planning? Stop forecasting? Stop projecting into the future? I think former President and General, Dwight D. Eisenhower had it right when he said, “In preparing for battle I have always found that plans are useless, but planning is indispensable.”

Embracing uncertainty doesn’t mean you stop planning. It means humbly having back up ideas of what to do if and when your plans prove wrong. Embracing uncertainty recognizes the limits of what we know. If you want a more detailed explanation of this idea, read Hayek’s Nobel acceptance speech, “The Pretense of Knowledge“. It is short and quite brilliant.

Embracing uncertainty means you should take all of the predictive nonsense with a healthy dose of skepticism. It means you need to build flexibility in yourself and your organization. The future will not resemble the past when the environment changes so quickly. Blackberry found that out ten years ago when Apple came out with the iPhone.

I will end with a snippet of a poem by Guillaume Apollinaire, Picasso’s friend that captures the entrepreneur well:

Come to the edge he said. They said: We are afraid. Come to the edge he said. They came. He pushed them, and they flew…